The Diary Of A CEO with Steven Bartlett
Former First Lady (Michelle Obama): This Is A Scam! People Were Running From Us Because We Were Black! I Was Bitter About The Racism I Received!
Thu, 01 May 2025
Michelle Obama served as the First Lady of the United States, entering the White House alongside Barack Obama. In this candid conversation, she joins Steven with her brother Craig Robinson, a former college basketball coach turned executive, to open up about everything from Trump’s inauguration to marriage challenges, grief, and rediscovering her purpose. Widely regarded as one of today’s most influential voices on leadership, identity, and social progress, Michelle offers a rare, intimate look at her personal journey. Together, they discuss: How their parents instilled empathy, discipline, and resilience growing up amid racial tension. Michelle’s journey through elite schools and corporate law, driven by a need to tick society’s boxes. The evolution of Michelle and Barack’s relationship, from colleagues to lifelong partners. Fertility struggles, parenting tips, and what it really takes to sustain a long-term marriage. Navigating life in the White House, grief, personal boundaries, and rediscovering her true calling. 00:00 Intro 02:11 Michelle and Craig's Childhood 04:48 Values Learned from Their Parents 08:45 Michelle Skipping Second Grade 12:16 The Role of Race in Their Childhood 15:19 What "White Flight" Means 17:01 Coping with Racism 20:55 Overcoming Being Underestimated 26:33 Michelle's Search for Identity 30:20 Meeting Barack 31:59 Introducing Barack to the Family 33:48 Why Michelle Initially Rejected Barack 37:28 Michelle's Career Change: Pursuing Joy 40:52 Relationship with Barack 44:56 Going to Counseling with Barack 49:34 Pregnancy Struggles 56:27 Hardest Moments in Their Marriage 57:31 Barack Obama Runs for Public Office 01:03:28 What I Should Have Said to Barack 01:07:11 Being the First Black First Lady and Facing Scrutiny 01:14:09 Reflections on a Sad Time 01:15:17 Remembering Your Mother 01:16:53 The Death of Your Mother 01:18:36 Processing the Grief 01:20:41 Not Attending Trump’s Inauguration Listen to Michelle & Craig's new podcast IMO: https://bit.ly/3YnxIUg Follow Michelle: Instagram - https://bit.ly/3Ymxs7W Twitter - https://bit.ly/4cYXiVC Follow Craig: Instagram - https://bit.ly/4lThkVB Twitter - https://bit.ly/4lTGJ1f You can purchase Michelle’s book, ‘Overcoming: A Workbook', here: https://amzn.to/4jTqcsi (UK) / https://amzn.to/3SbbelM (US) 100 CEOs: Ready to think like a CEO? Gain access to the 100 CEOs newsletter here: https://bit.ly/100-ceos-megaphone The 1% Diary is back - limited time only: https://bit.ly/1-Diary-Megaphone-ad-r… The Diary Of A CEO Conversation Cards (Second Edition): https://g2ul0.app.link/f31dsUttKKb Get email updates: https://bit.ly/diary-of-a-ceo-yt Follow Steven: https://g2ul0.app.link/gnGqL4IsKKb Sponsors: Airalo - https://try.airalo.com/TheDiaryOfACEO with code DOAC3Vivobarefoot - https://vivobarefoot.com/DOAC with code DIARY20 for 20% off Learn more about your ad choices. Visit megaphone.fm/adchoices
Chapter 1: What was Michelle Obama and Craig Robinson's childhood like on Chicago's South Side?
I find it incredibly fascinating that when we look at the back end of Spotify and Apple and our audio channels, the majority of people that watch this podcast haven't yet hit the follow button or the subscribe button, wherever you're listening to this. I would like to make a deal with you.
If you could do me a huge favor and hit that subscribe button, I will work tirelessly from now until forever to make the show better and better and better and better. Michelle, Craig. What do I need to know about your earliest context to understand the adults? And I use that word intentionally because I know that's what your parents were intent on raising.
The adults that are in front of me today.
It starts at 7436 South Euclid, the hub of it all. That was the home that we grew up in on the south side of Chicago. And it was a teeny tiny house. We lived above our Aunt Robbie. It was a single family home, a bungalow on the south side of Chicago. And our Aunt Robbie was married to her husband, Terry. And they owned the home.
And they had a little bitty, almost one-bedroom, two-bedroom apartment over the home. So it was a two-family home. We were surrounded by extended family. That community of people that you, probably because people didn't have a lot of resources, people lived with each other. You know, you shared spaces, you lived next to one another.
And we lived with our great aunt because it helped our parents save some money and get us in a better neighborhood. Because my father was a city worker. He was a working class guy, didn't have a college education. And working for the city was a really stable job because it gave you benefits and some stability there. And my mom wanted to stay home and raise kids.
So in order to save that kind of money, we band together and lived with our Aunt Robbie. And all of the adventures and the lessons learned, when I think about my foundational values, that house... Really, in all the experiences and conversations, the beginning of my kitchen table happened on 74th and Euclid. And I talk about it because you think it was a palace, but this was a little home.
We shared a bedroom most of our lives because there just wasn't room for us to each have our own room. And we shared the space, one bathroom. There was no dining room. There was just a kitchen.
And the way it was set up, how it was supposed to be used, it was a one-bedroom apartment. And the living room was the room that we shared as a bedroom. And the one bedroom it had was where my mom and dad lived. And the whole thing could have been 700 square feet.
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Chapter 2: What foundational values did Michelle and Craig learn from their parents?
Never took a sick day. He was the father that fathered all the other kids in the neighborhood. So when Craig was playing basketball, he was the person that was at most of the practices if he could be, if his shift allowed. He was the dad in the neighborhood where a lot of kids didn't have those kind of role models. And even though we didn't have a lot,
And there was never a time when my father wasn't going to help somebody. So I guess those values where you take care of people, money doesn't really matter. That's not the thing that makes you great. It's how you show up in the world. It's your word. It's how you treat other people.
to Misha's point, he was the guy who was giving kids rides to practice and to games because their parents couldn't go. And he would be sharing stories, sharing his values. It was just embedded in his being to pass on knowledge that he had. And with regard to my mom, You know, my mom, I think, is where, at least where I get my philanthropic gene from.
Not with money, because we didn't have any, but with our time and with our resource, whatever resources we had. What was behind all of this was unconditional love.
Mm-hmm. It's a tool in the toolbox that you sometimes don't even realize is there if you're privileged enough to. Right. Because it's that tectonic plate that sits underneath you that you never can really see, but gives you a certain sense of, I guess, risk and go get it.
Well, and knowing that, you know, it's not just unconditional love, but our parents believed us. They valued our voices. I mean, they really liked to hear us talk. They encouraged us to think out loud and to problem solve and to come to us with their problems but not be the ones that were going to solve it.
And this came in very handy when you're a kid in public school because, you know, in public school, south side of Chicago, teaching was kind of uneven. Right. You know, one year you'd get a teacher that cared and invested in the kids. Another grade, you'd have a teacher that didn't care. And I remember distinctly, I started second grade and I went to a classroom that was completely chaotic.
The teacher clearly didn't want to be there. And I knew this in second grade. And there was no order. We didn't have homework. We weren't doing regular lessons. And I knew that something was wrong. And I would come home at lunch and I'd complain about nothing happened today at school, you know. And I don't know what second grade is supposed to be.
But I don't feel like I'm getting what I need to get out of second grade. It took a month of coming home and complaining. And my mom was quietly listening. But she wasn't just listening. She was plotting. And it was a month in. She went up to the school, watched herself, and saw that this teacher not only wasn't teaching, but it appeared that she didn't even like kids.
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Chapter 3: How did race and 'white flight' shape Michelle Obama's early experiences?
I think our parents understood that that was waiting for both of us, and it was waiting for my brother in particular. So they wanted to arm him with enough self-esteem to fill him up at the table where he was safe, to give him the tools to just embed in him a level of empathy so that he wouldn't become angry, because anger for a young black boy was dangerous, you know? Yeah.
So there was a real clever way of allowing us to have these conversations but filling us up with empathy so that we could function in a racist society.
Being underestimated. It's a word that I saw throughout your book and it's a word you mentioned a second ago. You knew you were going into an underestimated world, if I can call it that, a world that was going to underestimate you because of your race and things like that. But it's so clear to me that you had your shoulders back regardless. And I spoke to Valerie.
Do you know Valerie?
Of course you know Valerie. You've worked with Valerie for many decades. She was sort of an early mental figure in your life, Michelle. Yes, she was. And she actually wrote me a letter about you. She describes that...
She's never met someone in her life that was so clear on what they wanted to achieve in the world in terms of the social good and the impact they wanted to have, but was so unbelievably confident and high conviction. And when I think about when you went to Harvard and studied law, there was what 30% of the people attending were women and then a tinier percentage were black women.
And you were aware again of being underestimated, but again, shoulders back, it seemed. Where does that come from in you?
Living through the incorrectness of that. of that underestimation, right? First of all, I grew up, you know, fortunately in a predominantly black neighborhood after white flight happened where everyone assumed I was smart, right? I grew up as the salutatorian in my grammar school. I went to a top high school. I, you know, so I had the fortune of growing up in a validating environment
Black environment, you know, which is, we talk about that a lot with Black students, whether they should be going to HBCUs and what happens when you get pulled out into a mixed environment where you are so underestimated so early. You know, you start, we talked about the messages that you start telling yourself. I didn't have that because when we were young, you know, I
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Chapter 4: How did Michelle Obama overcome being underestimated in elite academic environments?
Well, okay. Well, I met them. Wow.
Yeah.
I met them.
But they didn't meet mom and dad.
No, they didn't meet mom and dad, but that's because we weren't in Chicago.
Oh, anyway. All that matters is really how it turned out, right? This is the sibling. It's like, oh, you know.
You rejected him at first, right?
Yeah. Yeah, yeah, because Barack was—I was assigned to be his advisor. And that didn't mean I was his boss, but every—I was a first-year associate, so they tried to pair first years sort of with new summer associates just to— help get them acclimated and to kind of give them advice to sort of mentor them for the summer. So I was his mentor, mentor, right? So he comes in, he's late.
So I'm thinking, okay, this guy's trifling because we didn't in the Robinson family, we didn't do late, but he was raining and he didn't have an umbrella. And so he was a little wet. Um, So I was a little annoyed, but he stood up, and he was tall, and he was more handsome than his pictures. So I sort of thought, oh, okay, and not what I expected.
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Chapter 5: What identity crisis did Michelle Obama face as a corporate lawyer?
And when you're the president of the Harvard Law Review, basically the world of law is open to you. The normal path is that you clerk for an appellate judge. for a year or two, and then you go on to clerk for the Supreme Court. Then you go on to do appellate work. You have offers from every law firm. You are in demand, or you can do policy or whatever. That was the normal path.
I was like, so are you going to clerk? He was like, well, why would I clerk? So he didn't work at any of the big firms. He went to a very small firm that was doing public interest work. So he wasn't making a lot of money. He was doing what I was doing. He was going the opposite direction of all the things that were supposed to make us money. But he was like, money isn't why I'm doing this.
I'm trying to figure out how I can best use my skills to impact the most people. So he was doing... 50 million jobs. And we were cobbling together our payments for our student loans at the time, which were more than our mortgage. We had bought a condominium. We were on our way to building our lives together, but we were in deep debt.
So while we were both pursuing our deep love of being in the community, our incomes were going in the opposite direction of where they were supposed to go. But we were in this together. You know, politics hadn't really come into the fold yet. It wasn't a part of the conversation.
But we were both kind of on these parallel paths, kind of figuring out how do we take all these skills and all this energy and help people. I was working in the city. He was working everywhere else and writing a book. And we were just kind of, you know, we were sort of plotting ahead.
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I guess I'm seeking advice from both of you on love and romance and relationships because I'm in my early 30s now. And when I looked at both of your stories of love in your 30s, It's not a straight line. Oh, no. It's not a straight line, to say the least. Michelle, you talk about going to marriage counseling with Brock.
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Chapter 6: How did Michelle Obama meet Barack Obama and what was their early relationship like?
So when it happens to you, a box checker, somebody that thought life was going to be so and you did all the right things, to have things not work out and to know that it was going to be that way and nobody told you so that you could be prepared for it, it was a blow. And then as a woman, you're walking around owning the blow as if it's your fault. And so you're carrying around that burden.
And that can become the first pressure point in a marriage. Because emotionally, you've got a woman that is carrying all of this, feeling like a failure, not having anyone to talk about, having her hormones go up and down, literally. Probably dealing with depression and maybe some postpartum. Still working, still slaying dragons, still on the path, but she's carrying it all on her own.
And then if you do IVF, the bulk of the work, the shots, we are the petri dish in the IVF process. You show up, you come in a cup, and ooh, yay, good for you, right? And you're a little mad about that, too, because women have to get shots every week. And you have to go back and forth in between having your job, your high-powered job, and keeping it all together.
You're at the doctor's office every month trying to count your eggs and hoping that you're producing eggs, and then you have to go through the procedure. And then you have to be pregnant for nine months, right? As your partner is going to the gym and keeping his figure and, you know, all of that, you know.
So it's a long way of saying there are just many natural reasons why marriage, infertility, trying to have kids. makes things difficult. It's like, I try to tell couples, of course it's hard. Just listen to what I said, right? Like it's probably, if you're having some issues in your marriage, it's not you, it's the process of marriage.
It's just all hard because guess what happens when it all works out right? You know what you end up with? Babies. Little people with their own sense of everything. They mess you up. You love them dearly, but they're a hassle. And they're demanding. And they have their own whims. And now they're in your world, in your partnership. They are factored into everything.
So even when everything works out and you have the – 3.2 kids and you got everything right, it's still going to be hard because now you're developing a life, right? So I talk about these things because I think that people give up too quickly on marriage, right? because there is so much friction built in to the equation.
And if you're not getting help talking about it, going to therapy, just understanding how things are changing and how do you continuously renegotiate your relationship with your partner, I just see people quitting because they look at me and Barack and go, hashtag couple goals, you know? And I'm like, it's hard. It's hard for us too. But I wouldn't trade it.
You know, he is, as the young people say, he is my person.
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